CA1156264A - Method for the prevention of disturbances and/or the effects of disturbances in the preparation of hydrocarbon hydroperoxides by oxidation of hydrocarbons with molecular oxygen - Google Patents
Method for the prevention of disturbances and/or the effects of disturbances in the preparation of hydrocarbon hydroperoxides by oxidation of hydrocarbons with molecular oxygenInfo
- Publication number
- CA1156264A CA1156264A CA000367350A CA367350A CA1156264A CA 1156264 A CA1156264 A CA 1156264A CA 000367350 A CA000367350 A CA 000367350A CA 367350 A CA367350 A CA 367350A CA 1156264 A CA1156264 A CA 1156264A
- Authority
- CA
- Canada
- Prior art keywords
- oxygen
- reaction mixture
- disturbances
- temperature
- basic substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000003647 oxidation Effects 0.000 title claims abstract description 23
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 23
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 21
- 239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229910001882 dioxygen Inorganic materials 0.000 title claims abstract description 13
- 230000000694 effects Effects 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- -1 hydrocarbon hydroperoxides Chemical class 0.000 title claims abstract description 9
- 230000002265 prevention Effects 0.000 title claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 37
- 239000000126 substance Substances 0.000 claims abstract description 27
- 239000007789 gas Substances 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 11
- GWQOOADXMVQEFT-UHFFFAOYSA-N 2,5-Dimethylthiophene Chemical compound CC1=CC=C(C)S1 GWQOOADXMVQEFT-UHFFFAOYSA-N 0.000 description 10
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001527806 Iti Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/002—Avoiding undesirable reactions or side-effects, e.g. avoiding explosions, or improving the yield by suppressing side-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8000363 | 1980-01-21 | ||
| NL8000363 | 1980-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1156264A true CA1156264A (en) | 1983-11-01 |
Family
ID=19834710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000367350A Expired CA1156264A (en) | 1980-01-21 | 1980-12-22 | Method for the prevention of disturbances and/or the effects of disturbances in the preparation of hydrocarbon hydroperoxides by oxidation of hydrocarbons with molecular oxygen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4329514A (cs) |
| EP (1) | EP0032758B1 (cs) |
| JP (1) | JPS56118060A (cs) |
| BR (1) | BR8100288A (cs) |
| CA (1) | CA1156264A (cs) |
| DE (1) | DE3162543D1 (cs) |
| ES (1) | ES8200854A1 (cs) |
| ZA (1) | ZA81327B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH670821A5 (cs) * | 1987-03-24 | 1989-07-14 | Ciba Geigy Ag | |
| US4935551A (en) * | 1987-12-22 | 1990-06-19 | Indspec Chemical Corporation | Hydroperoxidation of diisopropylbenzene |
| US4950794A (en) * | 1989-05-24 | 1990-08-21 | Arco Chemical Technology, Inc. | Ethylbenzene oxidation |
| FR2708603B1 (fr) * | 1993-08-06 | 1995-10-27 | Rhone Poulenc Chimie | Procédé de préparation d'hydroperoxyde de cumène. |
| US6043399A (en) * | 1994-08-08 | 2000-03-28 | Rhodia Chimie | Process for the preparation of cumene hydroperoxide |
| CA2253215A1 (en) * | 1997-11-13 | 1999-05-13 | Shell Internationale Research Maatschappij B.V. | Process for preparing organic hydroperoxides |
| US6465695B1 (en) | 2001-07-27 | 2002-10-15 | General Electric Company | Method and system for manufacturing cumene hydroperoxide |
| RU2219169C1 (ru) * | 2002-07-29 | 2003-12-20 | Общество с ограниченной ответственностью "Петрофенол" | Способ получения гидроперекиси кумола |
| US7205376B2 (en) * | 2004-05-04 | 2007-04-17 | General Electric Company | Processes for the production of cumene, polyetherimides, and polycarbonates |
| CN116779047B (zh) * | 2022-03-11 | 2025-08-19 | 中国石油化工股份有限公司 | 苯硝化反应失控识别方法、识别系统及失控抑制方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA558506A (en) * | 1958-06-10 | G. Joris George | Cumene oxidation to hydroperoxide with nitrogenous catalysts | |
| US2447794A (en) * | 1945-01-30 | 1948-08-24 | Union Oil Co | Hydrocarbon peroxides |
| BE481560A (cs) * | 1947-04-01 | |||
| NL77402C (cs) * | 1951-07-03 | |||
| US2867666A (en) * | 1954-09-22 | 1959-01-06 | Monsanto Chemicals | Production of alpha-methylbenzyl hydroperoxide |
| US3160668A (en) * | 1961-06-19 | 1964-12-08 | Pittsburgh Chemical Company | Hydroperoxide formation |
| GB1228033A (cs) * | 1967-09-21 | 1971-04-15 | ||
| US4028423A (en) * | 1968-04-18 | 1977-06-07 | Sun Oil Company | Oxidation of aliphatic and alicyclic hydrocarbons |
| PL96763B1 (pl) * | 1974-10-12 | 1978-01-31 | Zaklady Azotowe F Dzierzynskie | Sposob zapobiegania awariom i/lub skutkom awarii systemu reakcyjnego utleniania weglowodorow w fazie cieklej pod cisnieniem gazami zawierajacymi tlen |
-
1980
- 1980-12-22 CA CA000367350A patent/CA1156264A/en not_active Expired
-
1981
- 1981-01-06 DE DE8181200008T patent/DE3162543D1/de not_active Expired
- 1981-01-06 EP EP81200008A patent/EP0032758B1/en not_active Expired
- 1981-01-19 BR BR8100288A patent/BR8100288A/pt not_active IP Right Cessation
- 1981-01-19 US US06/225,939 patent/US4329514A/en not_active Expired - Lifetime
- 1981-01-19 ES ES498618A patent/ES8200854A1/es not_active Expired
- 1981-01-19 ZA ZA00810327A patent/ZA81327B/xx unknown
- 1981-01-19 JP JP521581A patent/JPS56118060A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0032758A2 (en) | 1981-07-29 |
| BR8100288A (pt) | 1981-08-04 |
| EP0032758A3 (en) | 1981-08-26 |
| DE3162543D1 (en) | 1984-04-19 |
| JPH0258263B2 (cs) | 1990-12-07 |
| JPS56118060A (en) | 1981-09-16 |
| ES498618A0 (es) | 1981-11-16 |
| ES8200854A1 (es) | 1981-11-16 |
| EP0032758B1 (en) | 1984-03-14 |
| ZA81327B (en) | 1982-02-24 |
| US4329514A (en) | 1982-05-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |